Calcium Carbonate → N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamine

HRID 2108548Notes

Reaction equation

HRID 2108548 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][CH:6]([CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:4].C([O-])([O-])=O.[Ca+2].[I:24]Cl>CO>[F:1][C:2]([F:17])([F:18])[C:3]([NH:5][CH:6]([CH3:16])[CH2:7][C:8]1[CH:9]=[C:10]([O:14][CH3:15])[CH:11]=[CH:12][C:13]=1[I:24])=[O:4]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 24640Iodine chlorideHCID 14964390N-(Trifluoroacetyl)-1-(3-methyloxyphenyl)propan-2-ylamine

Product 1

HCID 86590367N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamineYield 110.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of N-trifluoroacetyl-1-(3-methoxyphenyl)-2-propylamine (4.29 g, 15.7 mmol) in methanol (100 mL) was cooled to −78 C and treated with CaCO3 (3.17 g, 31.4 mmol), followed by a solution of ICl (6.37 g, 39.3 mmol) in methanol (50 mL). The reaction was allowed to warm to 20 C while stirring overnight. The product mixture was filtered, concentrated, dissolved in EtOAc (200 mL), washed twice with 5% aqueous sodium bisulfite (100 mL), once with brine (100 mL), dried with Na2SO4 and concentrated to give 6.72 g of a white solid powder. MS calculated for C12H13F3INO2+H: 388, observed: 388.

Workup

  1. temperatureto warm to 20 C
  2. filtrationThe product mixture was filtered
  3. concentrationconcentrated
  4. dissolutiondissolved in EtOAc (200 mL)
  5. washwashed twice with 5% aqueous sodium bisulfite (100 mL), once with brine (100 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-67890946fe2b4f628c18cfa4f0bff602
Source dataset
uspto-grants-2009_04
Patent number
US07514422B2

Reaction notes

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